Total synthesis of guaianolides:(.+-.)-dehydrocostus lactone and (.+-.)-estafiatin

JH Rigby, JAZ Wilson

Index: Rigby,J.H.; Wilson,J.Z. Journal of the American Chemical Society, 1984 , vol. 106, p. 8217

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Citation Number: 59

Abstract

Abstract: The total synthesis of two guaianolide sesquiterpenes,(A)-dehydrocostus lactone and (f)-estafiatin, is described. The synthesis starts with 2, 4, 6-cycloheptatrien-l-one (tropone) and introduces the elements of the five-membered ring through a 1, 8-addition of the Grignard reagent derived from 2-(2-bromoethyl)-l, 3-dioxolane. A stereocontrolled Lewis acid mediated cyclization reaction generates the requisite cis-fused hydroazulene ...